Synthesis and in vitro antitumor activity of naringenin oxime and oxime ether derivatives

Ahmed Dhahir Latif, Tímea Gonda, Mátë Vágvölgyi, Norbert Kúsz, Ágnes Kulmány, I. Ocsovszki, Zoltán Pëter Zomborszki, I. Zupkó, Attila Hunyadi

Research output: Contribution to journalArticle

Abstract

Naringenin is one of the most abundant dietary flavonoids exerting several beneficial biological activities. Synthetic modification of naringenin is of continuous interest. During this study our aim was to synthesize a compound library of oxime and oxime ether derivatives of naringenin, and to investigate their biological activities. Two oximes and five oxime ether derivatives were prepared; their structure has been elucidated by NMR and high-resolution mass spectroscopy. The antiproliferative activity of the prepared compounds was evaluated by MTT assay against human leukemia (HL-60) and gynecological cancer cell lines isolated from cervical (HeLa, Siha) and breast (MCF-7, MDA-MB-231) cancers. Tert-butyl oxime ether derivative exerted the most potent cell growth inhibitory activity. Moreover, cell cycle analysis suggested that this derivative caused a significant increase in the hypodiploid (subG1) phase and induced apoptosis in Hela and Siha cells, and induced cell cycle arrest at G2/M phase in MCF-7 cells. The proapoptotic potential of the selected compound was confirmed by the activation of caspase-3. Antioxidant activities of the prepared molecules were also evaluated with xanthine oxidase, DPPH and ORAC assays, and the methyl substituted oxime ether exerted the most promising activity.

Original languageEnglish
Article number2184
JournalInternational journal of molecular sciences
Volume20
Issue number9
DOIs
Publication statusPublished - May 1 2019

Fingerprint

Oximes
Ether
Ethers
ethers
Derivatives
synthesis
activity (biology)
cancer
Cells
xanthines
multiple docking adapters
Bioactivity
cycles
leukemias
oxidase
Assays
antioxidants
apoptosis
cells
cultured cells

Keywords

  • Antioxidant
  • Antiproliferative
  • Caspase activity
  • Cell cycle analysis
  • Naringenin derivative
  • Naringenin-oxime
  • Oxime ether

ASJC Scopus subject areas

  • Catalysis
  • Molecular Biology
  • Spectroscopy
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Synthesis and in vitro antitumor activity of naringenin oxime and oxime ether derivatives. / Latif, Ahmed Dhahir; Gonda, Tímea; Vágvölgyi, Mátë; Kúsz, Norbert; Kulmány, Ágnes; Ocsovszki, I.; Zomborszki, Zoltán Pëter; Zupkó, I.; Hunyadi, Attila.

In: International journal of molecular sciences, Vol. 20, No. 9, 2184, 01.05.2019.

Research output: Contribution to journalArticle

Latif, Ahmed Dhahir ; Gonda, Tímea ; Vágvölgyi, Mátë ; Kúsz, Norbert ; Kulmány, Ágnes ; Ocsovszki, I. ; Zomborszki, Zoltán Pëter ; Zupkó, I. ; Hunyadi, Attila. / Synthesis and in vitro antitumor activity of naringenin oxime and oxime ether derivatives. In: International journal of molecular sciences. 2019 ; Vol. 20, No. 9.
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